Orlando Academy: every transfer in and out, fees paid and earned, squad market value.
| Date | Player | From | To | Fee |
|---|---|---|---|---|
| 2025-02-13 | Justin Ellis | Orlando Academy | Orlando City B | — |
| 2024-09-01 | Ryan Basabe | Orlando Academy | IDA Valencia | — |
| 2024-08-01 | Majed Abdullah | Orlando Academy | Al-Shabab U19 | Free |
| 2024-04-24 | Colin Guske | Orlando Academy | Orlando City B | — |
| 2024-03-15 | Majed Abdullah | Orlando Academy | Orlando City B | Loan |
| 2024-03-15 | Justin Ellis | Orlando Academy | Orlando City B | Loan |
| 2024-03-15 | Colin Guske | Orlando Academy | Orlando City B | Loan |
| 2024-03-12 | Zakaria Taifi | Orlando Academy | Orlando City B | — |
| 2024-01-23 | Tahir Reid-Brown | Orlando Academy | Orlando | — |
| 2023-08-14 | Gustavo Caraballo | Orlando Academy | Orlando City B | — |
| 2023-03-21 | Zakaria Taifi | Orlando Academy | Orlando City B | Loan |
| 2023-03-21 | Tahir Reid-Brown | Orlando Academy | Orlando City B | Loan |
| 2023-03-21 | Alejandro Granados | Orlando Academy | Orlando City B | — |
| 2023-01-01 | Justin Ellis | Miami Academy | Orlando Academy | Free |
| 2022-03-24 | Tahir Reid-Brown | Orlando Academy | Orlando City B | Loan |
| 2022-03-24 | Moises Tablante | Orlando Academy | Orlando City B | — |
| 2022-03-24 | Javier Otero | Orlando Academy | Orlando City B | — |
| 2022-03-24 | Alejandro Granados | Orlando Academy | Orlando City B | Loan |
| 2022-02-15 | Alex Freeman | Orlando Academy | Orlando | — |
| 2021-06-15 | Thomas Williams | Orlando Academy | Orlando | — |